Entourage[3] is a hit HBO television series about Vince Chase, a Hollywood superstar, and his band of merry men that includes his older brother Johnny “Drama,” his manager Eric “E” Murphy, and the butt of all jokes, Turtle. It’s loosely based on Mark Wahlberg’s experiences as an up and coming actor and he’s one of the show’s executive producers.

I started watching the series after friends told me it was a lot of fun to watch. I’ve made it through the first few seasons (they started shooting Season 5 last spring) and I have to say it’s a really entertaining show. There are a ton of celebrity cameos and seeing the lifestyle, however fictionalized, makes for a good half hour escape. It’s not surprising that it’s a popular show.

So, what does it have to do with personal finance? Well, money management is interwoven into our lives and it’s no different for a fictitious actor. With his rise to stardom comes fame and fortunate and many of the episodes touch on how they deal with the money. I wanted to just pull out a few of those lessons to share with you all.

#1. Don’t Count Your Chickens

In Season One, prior to the launch of Vince’s blockbuster Aquaman, they go out and buy a four million dollar mansion. Their financial adviser had given them a budget of “only” a million but on a whim they blew right through it. As ridiculous as that sounds, the lesson you can learn from this, and the ensuing angst, is a lesson that’s been taught for centuries. Don’t count your chickens before they’ve hatched.

That promotion you’re sure you’ll be getting this year, or that fat raise, or just that bonus… you might not get it. Or maybe you’ll get it three months after you expect it, or six months. The economy can change very quickly and business cycles have a way of cycling the wrong way, so it’s important that you never commit to things until that “sure thing” actually comes through. If you do commit before you should, even a 1% chance that something won’t come through will cause you a tremendous amount of undue stress.

#2. Be Creative

In an episode titled “Good Morning Saigon” in the second season, the group finds their Maserati’s been stolen (what a horrible life they lead!). When they get it retrieved, they discover a mixtape CD from a rapper named Saigon (Saigon is real[4]). Turtle manages to get one of the tracks used in the end credits of “Queens Boulevard,” a fictional Sundance nominated indie film. Eventually, Turtle represents Saigon and gets him a record deal.

While I’m not advocating that you break into expensive cars and drop your mixtape CD, the lesson here is that you need to use some creativity if you want to separate yourself from the pack. I’ve heard stories of people sending pizzas and donuts with their resume to companies where they’ve wanted jobs. Doing something that separates you from all the other prospects, especially something that establishes a connection or a relationship, is going to get you a leg up in almost anything you do.

#3. Don’t Make Emotional Decisions

Over the course of several episodes in Season Two, Vince gets back together with his first love, Mandy Moore, prior to the start of shooting for Aquaman, a movie where Mandy Moore is a co-star. Mandy was engaged, she broke up with her fiance, started going out with Vince, then she got back with her fiance. The end result is that Vince’s heart is shattered and he wants to quit Aquaman. He’s eventually dissuaded by his childhood friend E, who became his manager in Season One, and the movie ends up grossing more than Spider-Man on opening weekend.

Decisions are best made when emotions are not involved. Stock market takes a 400 point nosedive? Relax, don’t freak out… decide what you want to do when you know you’ve calmed down(don’t know if you’ve calmed down? ask a close friend!). Every emotion has a way of clouding your judgment. Really happy? You’ll make bad decisions because you’re too optimistic. Annoyed? You’ll make bad decisions because you want to reduce all your hassles and headaches. Angry? You’ll make all sorts of irrational decisions this way.

#4. Reward Others

Vince often buys the other guys lavish gifts like motorcycles, cars, etc. He lets them live in his enormous mansion, takes them on meets, and otherwise takes very good care of them throughout the show. Even Saigon, the rapper, bought Turtle some CZ bling after a record deal (a deal that all started when Vince used his connections to get a popular radio DJ to play a Saigon track).

The lesson here is that you should reward those who help you get to where you are. If you’re in management, reward the people who work with on a regular basis to show your appreciation. You don’t have to get them motorcycles or cars, but an occasional thank you, some nice chocolates or candy, and other small tokens of appreciation are always… well, appreciated.

#5. Trust Is Priceless

After the success of Aquaman, Ari Gold, Vince’s agent, dumps about half a dozen multi-million dollar acting offers into the trash (should’ve been a recycling bin!) in order to connect Vince with a project he’s always wanted to do: Medellín. Medellín was to be the story of Pablo Escobar. Anyway, fast forward and there’s a scheduling conflict with Aquaman 2, a promise is made and then broken by Alan Gray (head of Warner Brothers Studio, maker of Aquaman), and a pissed off actor. The end result is that a pissed off Gray ups his offer, Vince relents and accepts, but skips a breakfast meeting that gets him replaced on Aquaman 2. Medellín also falls through as they decide to go with Benicio Del Toro instead (kind of funny because Del Toro is working on Che[5], a biopic about revolutionary Che Guevara, in real life).

The whole point of this was that doing the film wasn’t about the money, it was about a promise that was broken. Gray had promised Chase that he’d push back production on Aquaman 2 so that Chase could work on his dream project. Gray eventually backed out on his word, which pissed off Chase. On one hand, you could go back to how you shouldn’t let emotion cloud your judgment but on the other hand, it’s often more about principles than it is money. Trust is more important than money and in this case and once you lose it, no amount of money can get it back.

#6. Follow Your Passion

Getting back to Medellín, eventually Chase and E (Eric Murphy, Chase’s manager) scrape up some cash and buy the script after the movie falls apart. Many episodes in Season Three and Four are devoted to Chase and E working towards getting this project finished, including working with the mercurial Billy Walsh (he directed Queens Boulevard from Season One). The end result is that the film is made and Vince finally gets the project he’s been dreaming about for several years.

The lesson here is that you need to follow your passions to the bitter end. To buy the script, Chase and E sell practically all their possessions, including the aforementioned four million dollar home. Some would say that’s plain stupid, but I think that if you’re passionate about something than you have to go at it 100%. If you hold anything back, you’ll always wonder “what if?” Isn’t it better to have loved and lost, than to have never loved at all?

If you have a few hours days to kill (or a long flight somewhere), check out Entourage, it’s a fun show. Season Five just started so you better get moving if you want to catch up! (thanks Walt!)